“Describe a time when…” Interview Questions

I have had quite a lot of interviews this year and I want to gather some of my observations. Hopefully this will help both you and I prepare for the next one.

Very often interviewers want stories with specific examples, and if you haven’t planned for that it’s hard to come up with an example. On my resume, for example, I say I’m particularly good at debugging code. And that’s true. I have successfully investigated and solved so many software bugs that to me at this point it’s all rather a blur. Recently, then, I have been asked on two separate occasions to remark on specific bugs I faced. The first time that happened, I was caught completely off guard. I was able to speak in generalities, but I had never committed the specific details of any particular case to memory. So… I floundered a bit. I tried to make my generalities as specific as possible, and to ground them solidly in concrete hypothetical scenarios. But I know that didn’t land as well as if would have if I’d had a real story ready to go.

More recently, I had a final-round interview with a company that consisted entirely of something like 15 of those “describe a time when…” type questions, one after another. Most of them were not programming specific, but obviously just for the sake of staying on topic it’s best to choose stories from one’s professional experience.

The methods behind some interview processes are secretive because the interviewer wants to surprise the candidate in some way, give them some kind of test and see how they respond. I don’t think these HR type questions they asked me in my most recent interview are considered confidential, and I don’t think it’s unethical in any way to share some of the specifics of this interview process with you, so I will share some of it.

They asked me several very generic questions. I’ll paraphrase a few from memory.

• Describe a time when you had to learn something quickly. How did you do it, were you successful, etc.
• Describe a time when a supervisor asked you to do something you thought was “wrong”? What did you do? (They had options ready to go in case this had never happened to me.)
• Describe a time when you suggested some new idea or initiative to a supervisor. How was it received, what happened, etc?
• Describe a time when you had to make some abrupt change (at work). How did you handle that?
• Describe a time when you responded to a situation too quickly or too slowly. What was the result?

For some of these, I had a story ready to go. For several of these questions, I had no story. I had to dance. For some of them, I was able to put together a relevant example on the fly. For others, I talked for a few minutes and even I thought I strayed pretty far off topic. (I wonder if they noticed.)

A few of them were completely irrelevant and I just passed. For example, there has just never been a situation where I had to make some critical decision at work very quickly. They ask that one a lot. It depends what you mean by critical, right? Since I have never been a surgeon or a fighter pilot, I just don’t think in my professional life I’ve ever had to make any critical decision quickly—ever. I’ve definitely never had to make a decision with a ticking clock counting down until someone dies. So… I’m not willing to call anything I do “critical”. Passing is an option even if they don’t tell you it is. The only problem is that it may or may not be well received.

Something I’ve learned from this experience, is that I need to actively build a collection of stories to tell during interviews. I’m well aware this isn’t new advice. I’ve seen similar advice in books about interviewing well, but I guess it didn’t sink in enough for me to actually do it. What I’m talking about here is a very detailed and methodical process. Very likely, I’m going to put them on paper. I’m going to think over scenarios from my work history and write them down as small, self-contained narratives. I’m not going to write them in such a way as to be answers to specific questions. Rather, a single story could be an answer to various different questions. And you can always sneak in favorable facts about yourself into every story. Favorable facts are the best kind of facts.

Just as a result of the interviews I have been through so far, I already have a few of these narratives in a bank ready to go at a moment’s notice. Based on recent interview questions, now I see some holes in my collection of stories that need to be filled. I need a story of a time when I helped a colleague understand something and there was clear indication that he or she understood better afterward. And others.

Oy. Interviews are exhausting, no? Happy story-telling.